NAV

(2E)-1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Identification

Generic Name
(2E)-1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
DrugBank Accession Number
DB07500
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 338.397
Monoisotopic: 338.151809192
Chemical Formula
C21H22O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGroup IIE secretory phospholipase A2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Chalcones and dihydrochalcones
Direct Parent
3-prenylated chalcones
Alternative Parents
2'-Hydroxychalcones / Cinnamylphenols / Hydroxycinnamic acids and derivatives / Methoxyphenols / Anisoles / Aryl ketones / Benzoyl derivatives / Styrenes / Phenoxy compounds / Methoxybenzenes
show 7 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2'-hydroxychalcone / 3-prenylated chalcone / Acryloyl-group / Alkyl aryl ether / Alpha,beta-unsaturated ketone / Anisole / Aromatic homomonocyclic compound / Aryl ketone / Benzenoid
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Chalcones and dihydrochalcones (LMPK12120046)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZUGCRBMNFSAUOC-YRNVUSSQSA-N
InChI
InChI=1S/C21H22O4/c1-14(2)4-8-16-12-18(20(24)13-21(16)25-3)19(23)11-7-15-5-9-17(22)10-6-15/h4-7,9-13,22,24H,8H2,1-3H3/b11-7+
IUPAC Name
(2E)-1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES
COC1=CC(O)=C(C=C1CC=C(C)C)C(=O)\C=C\C1=CC=C(O)C=C1

References

General References
Not Available
PubChem Compound
5321765
PubChem Substance
99443971
ChemSpider
4479431
BindingDB
246523
ZINC
ZINC000019816069
PDBe Ligand
BVL
PDB Entries
2zbh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00322 mg/mLALOGPS
logP4.49ALOGPS
logP5.5Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)7.07Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area66.76 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity101.54 m3·mol-1Chemaxon
Polarizability37.26 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9781
Blood Brain Barrier-0.6568
Caco-2 permeable+0.8105
P-glycoprotein substrateSubstrate0.6936
P-glycoprotein inhibitor IInhibitor0.5522
P-glycoprotein inhibitor IIInhibitor0.7256
Renal organic cation transporterNon-inhibitor0.8045
CYP450 2C9 substrateNon-substrate0.7783
CYP450 2D6 substrateNon-substrate0.8473
CYP450 3A4 substrateSubstrate0.622
CYP450 1A2 substrateInhibitor0.8444
CYP450 2C9 inhibitorInhibitor0.7744
CYP450 2D6 inhibitorNon-inhibitor0.6658
CYP450 2C19 inhibitorInhibitor0.9503
CYP450 3A4 inhibitorNon-inhibitor0.7365
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9044
Ames testNon AMES toxic0.9159
CarcinogenicityNon-carcinogens0.8354
BiodegradationNot ready biodegradable0.8908
Rat acute toxicity2.2755 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9251
hERG inhibition (predictor II)Non-inhibitor0.8271
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0259000000-2771eed2a5bf78ed7b03
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-0095000000-3e0714fcb2534d7d8a73
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0629000000-a254aa9658a60575425f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-1948000000-f15c43b1264e36587c2d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0972000000-b4d257a828ad06df7561
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0wml-2911000000-e9a8d93bf610b8647fce
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-211.7762382
predicted
DarkChem Lite v0.1.0
[M-H]-188.46379
predicted
DeepCCS 1.0 (2019)
[M+H]+211.9472382
predicted
DarkChem Lite v0.1.0
[M+H]+190.86107
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.6492382
predicted
DarkChem Lite v0.1.0
[M+Na]+198.05133
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Group IIE secretory phospholipase A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name
PLA2G2E
Uniprot ID
Q9NZK7
Uniprot Name
Group IIE secretory phospholipase A2
Molecular Weight
15988.525 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:23 / Updated at June 12, 2020 16:52